Methylamine hydrochloride → HCID 15886822, compound

HRID 1602856Notes

Reaction equation

HRID 1602856 reaction equation
Cl.[CH3:2][NH2:3].O=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3([N:27]4[CH2:32][CH2:31][N:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH2:29][CH2:28]4)[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]3)[CH:15]=2)=[O:12])[CH2:7][CH2:6]1>C1COCC1.CO>[CH3:2][NH:3][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3([N:27]4[CH2:28][CH2:29][N:30]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:31][CH2:32]4)[CH2:21][CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25]3)[CH:15]=2)=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6364545Methylamine hydrochloride2×HCID 9869513HCID 9869513, compound

Product 1

HCID 15886822HCID 15886822, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methylamine hydrochloride (37 mg, 0.546 mmol) was added to a solution of 4-(oxo)-N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer) (43 mg, 0.091 mmol) in THF/MeOH (1:1) and stirred at room temperature. When all the methylamine hydrochloride had dissolved, NaCNBH4 (6 mg, 0.091 mmol) was added and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated, dissolved in an excess of 3N HCl, and the aqueous solution washed with ether (3×). The aqueous solution was made basic with 10N NaOH, extracted with EtOAc (4×), dried (Na2SO4), and concentrated to give 4-(methylamino)-N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)-cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer) as a clear oil. The HCl salt was prepared by adding excess saturated EtOAc/HCl solution to the free base in dry MeOH. Concentration of the homogeneous solution yielded a white solid which was washed with EtOAc. mp=154-155° C.

Workup

  1. additionNaCNBH4 (6 mg, 0.091 mmol) was added
  2. stirringto stir overnight at room temperature
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in an excess of 3N HCl
  5. washthe aqueous solution washed with ether (3×)
  6. extractionextracted with EtOAc (4×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ece05cc3d4f84a529b13e0ecb7513957
Source dataset
uspto-grants-1999_11
Patent number
US05985873

Reaction notes

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